Ethanol → 6-Ethoxy-4,5-dimethylpyridazin-3-amine

HRID 1501348Notes

Reaction equation

HRID 1501348 reaction equation
Cl[C:2]1[N:7]=[N:6][C:5]([NH2:8])=[C:4]([CH3:9])[C:3]=1[CH3:10].[CH2:11]([O-:13])[CH3:12].[Na+].C(O)C>>[CH2:11]([O:13][C:2]1[N:7]=[N:6][C:5]([NH2:8])=[C:4]([CH3:9])[C:3]=1[CH3:10])[CH3:12]

Participants

4

Reactant 3

HCID 702EthanolHCID 2723922Sodium ethoxideHCID 69919433-Amino-6-chloro-4,5-dimethylpyridazine

Product 1

HCID 867165186-Ethoxy-4,5-dimethylpyridazin-3-amineYield 50%

Procedure

6-Chloro-4,5-dimethylpyridazin-3-amine (CAS-Nr. 76593-36-7, 500 mg, 3.17 mmol, 1.0 eq) and sodium ethanolate in ethanol (16 mL, 21 w/w-%, 53.9 mmol, 17 eq) were heated for 2 h to 130° C. in a single mode microwave oven. The reaction mixture was partitioned between DCM and water. The organic phase was washed with brine and dried with sodium sulfate. The resulting mixture was filtered through a Whatman filter and the volatile components were removed in vacuo. The crude mixture was purified via MPLC (Biotage Isolera; 28 g NH2-cartridge: hexane→hexane/EtOAc 1/1) to give 267 mg (50% yield) of the title compound.

Workup

  1. customThe reaction mixture was partitioned between DCM and water
  2. washThe organic phase was washed with brine
  3. dry with materialdried with sodium sulfate
  4. filtrationThe resulting mixture was filtered through a Whatman
  5. filtrationfilter
  6. customthe volatile components were removed in vacuo
  7. customThe crude mixture was purified via MPLC (Biotage Isolera; 28 g NH2-cartridge: hexane→hexane/EtOAc 1/1)

Sources & evidence

ORD record
ord-4bd2f3380f4e4e51a356f6fce355d5b8
Source dataset
uspto-grants-2015_12
Patent number
US09206185B2

Reaction notes

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